Visit the Legendary Windy City
Head to Chicago, Cook County's vibrant country seat: The iconic Magnificent Mile, Millennium Park, the Riverwalk - this city will have you snapping photo after photo! Enjoy world-class shopping, superb architecture and fabulous museums. Finish your day with some famous deep-dish pizza at a fabulous rooftop restaurant with views of Chicago's amazing skyline.

Timeless and opulent, few other hotels in America have as much legendary acclaim as the famous Drake Hotel. Located at the Gold Coast end of Michigan Avenue, this historic hotel hosted the likes of Marilyn Monroe and Joe DiMaggio (who carved their initials at the bar after they were married) and countless other stars and notables since the roaring twenties. Step inside and let its elegant design take you back to an era of days gone by.

Sample dates: November 2026
More dates are available (prices may vary): 09/26/2026 to 04/28/2027

Our Hotel Pick: 4* The Drake
• Destination: Downtown Chicago, Cook County, Illinois
• Rating: Very good 4.2/5 TripAdvisor Traveler rating with Travelers' Choice Award
• What's around: Magnificent Mile, 360 Chicago, Chicago Lakefront Trail
• What's included: free Wi-Fi
• Amenities: restaurant, bar, café, piano lounge, 24-hour front desk, luggage storage, fitness center, valet parking.
• Duration: 2 nights
• Hotel price: from $129 per person (based on double occupancy)

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